The present invention relates to a method for manufacturing 3,4,5-tricaffeoylquinic acid.
In recent years, research and development on the utilization of plant resources is being conducted in a variety of fields have been performed.
Among them, polyphenols in particular are attracting attention from the viewpoint of health care, and various polyphenols are extracted from plants and are utilized in various applications. For example, it has been reported that sweet potato-derived polyphenols are effective in diseases and beauty care, such as cancers, diabetes mellitus, hypertension, Alzheimer's disease, HIV, and melanogenesis inhibition (Shokuhin Kogyo (Food Industry), Vol. 3 (2005), pp. 1-7 (Shokuhin Gijutsu Tosho Shuppan)).
Chlorogenic acids, which constitute one class of polyphenols, are contained in coffee beans, sweet potato leaves, mugwort, honeysuckle, sunflower, and the like, and chlorogenic acids have been extracted from plants using hot water or ethanol. However, it has been extremely difficult to purify chlorogenic acids to such a high extent that the purified chlorogenic acids can be utilized as pharmaceutical products.
3,4,5-Tricaffeoylquinic acid has the highest physiological activity among chlorogenic acids, and it has been reported that this acid has various physiological activities such as strong antitumor action, antidiabetic action, antihypertensive action, and antiviral action (Shokuhin to Gijutsu (Food and Technologies), Vol. 8 (2008), pp. 10-18 (Japan Food Industry Center)). 3,4,5-Tricaffeoylquinic acid is obtained by extracting the acid from the stems and leaves of sweet potato or Brazilian propolis using an alcohol, subsequently degreasing the extract with hexane, and fractionating the acid by adsorption chromatography and gel filtration chromatography (JP 2005-298382A).
However, the amount of 3,4,5-tricaffeoylquinic acid contained in plants and the like is so small that, in order to obtain highly pure 3,4,5-tricaffeoylquinic acid, a complicated and long purification process is required. In spite of having attractive physiological activity, it has been difficult to apply 3,4,5-tricaffeoylquinic acid to practical applications.
On the other hand, synthesis of 3,4,5-tricaffeoylquinic acid has been investigated, and the complete synthesis was reported for the first time in Chem. Pharm. Bull., Vol. 59 (2011), pp. 502-507.